We have a secret to share. We totally ignore the Common App essay prompts. It doesn’t matter which kid we are working with or what kind of story they have to share. We believe in starting with a blank page—not a prompt. However, we also know that not every kid gets to work with us 1) because we are a specialized service and 2) because there are just so many hours in a day and only so many days before applications are due. We started this blog so that we could speak to the kids who don’t have a hands-on helper during this process, and we understand that, like our posts, the Common App essay prompts may not make it smooth sailing, but they do give you a place to start.

We’ve already analyzed the first essay prompt, so here we’re going to dive into the second.

The lessons we take from obstacles we encounter can be fundamental to later success. Recount a time when you faced a challenge, setback, or failure. How did it affect you, and what did you learn from the experience?

Pretty simple, right? Well...not quite. As we’ve said, we ignore the prompts. Yes, we could just say that we pick #7 (the “do whatever you want” option), but that would imply that we even consider numbers 1-6. But if we were to consider the prompts and end up picking #2, this would be our roadmap to answering it.

Q: Why would you ever pick this prompt?

A: A lot of people avoid this prompt because the idea of writing about an obstacle (which is a code word for ‘failure’) is horrifying. We get that. When you’re a teenager, any failure can feel catastrophic, even the tiny ones. If you can get over the fear factor, this prompt does offer some room to play. Why? Because it’s designed to be answered with a story. We’re obsessed with stories, and you should be too. The benefit of writing about challenges is that it’s like having a story arc passed down to you by the college admissions gods. Struggles come with breakthroughs, and breakthroughs come with ah-ha moments, and all three of those things make for great essays. So, to answer the question, you would pick this prompt if you want to tell a story that has a serious arc to it.

Q: If it’s so easy, what could go wrong?

A: Hold up a sec. We never said it would be easy and there are lots of ways in which it could go completely haywire.

Q: Ok, so it’s possible to mess up. But how, exactly?

A: Here are three common traps that people fall into…

They write about something that isn’t really a failure at all.

As we’ve acknowledged, writing about obstacles, hurdles, and failure can be uncomfortable. One way that people try to assuage this discomfort is by picking a failure to focus on that isn’t a failure in the first place. Messy handwriting may be frustrating, but it’s not a failure. Struggling at track before realizing that you’re a pole vaulting wizard is not failing. Being really good at math and taking every course your school offers so having nothing else to challenge you is not a failure. These examples may all have involved periods of frustration or struggle, but they are nothing to write home about, and thus nothing to write your essay about.

If you are going to pick this prompt, you need to be willing to spotlight a time that you unabashedly failed. You fell flat on your face in the final lap of the championship 3000-meter race. You spelled ‘spelling’ wrong in a school bee (that second ‘l’ proved to be a trickster thanks to the stress). Your dream of becoming a scuba diver was thwarted by the discovery that being underwater triggers panic attacks. And then no, you don’t overcome the fear to become a famous diving pro. You learn something, you develop as a person, you have something to say, but you don’t blossom into a perfect flower. The lawnmower ran over you, and you had to find a way to put your pieces back together.

Cheesy language sneaks in.

“And then I realized that the world is a beautiful place.”

“Afterwards, I came to learn that my greatest strength is self-love.”

“In the end, all that matters is enthusiasm.”

You know those sentences. They are the ones that make you cringe to write in any other format and yet somehow end up flowing from your fingers as soon as you open your college essay document. They are painful, we refuse to let them wiggle their way into our essays, and if this prompt has a magical power it is drawing these sentences out of even the most cynical student.

Privilege oozes out of the woodwork.

Every person goes through struggles, but there is something about this prompt that inspires privileged kids to talk about the time they were burdened with a beat-up car for their 16th birthday (dude, you still got a free car), or when they didn’t get elected captain of the soccer team (but it’s ok, they were the top goal-scorer anyway). These are terrible answers because they scream privilege. The desire to highlight petty problems is unique to people who don’t have to face deeper challenges like housing issues, family instability, food insecurity, and financial distress. Having it (relatively) easy doesn’t make you a bad person, but it does mean that you shouldn’t use your college essay to focus in on something that would be a walk in the park for many others.

The Verdict

If you have faced serious challenges that you feel need to be illustrated in your application, this prompt is a good option for you. Just remember that you need to include a clear story arc, a strong narrative, and please please please avoid cheesy, “and then I realized!” sentences.

If you have a complicated story to tell, consider dropping us a line. We’re experts in turning complex stories into compelling admissions-winning essays.